Acylation of Arylamines with Triethylamine Derivatives in Combination with tert-Butyl Hydroperoxide

被引:5
作者
Chen, Cui [1 ]
Liu, Weibing. [1 ]
Liu, Bifu. [2 ]
Zhou, Peng [1 ]
Tan, Hua [1 ]
机构
[1] Guangdong Univ Petrochem Technol, Coll Chem, 2 Guandu Rd, Maoming 525000, Peoples R China
[2] Huizhou Univ, Sch Chem & Mat Engn, Huizhou 516007, Peoples R China
基金
中国国家自然科学基金;
关键词
alkyl transfer; N-dealkylation; N-acylation; trialkyl amines; C-N BOND; AMIDE; ALCOHOLS; ANNULATION; ALDEHYDES; CATALYST; PEPTIDE; ACCESS;
D O I
10.1002/ajoc.201900119
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-acylation of arylamines with di- and trialkyl amines has been reported. This approach provides a general synthesis of aromatic amides by an alkyl transfer through cleavage of the C-N bond, and acts as a model for N-dealkylations and N-acylations. Additionally, the synthesis is a promising method towards amidation reactions, wherein di- and trialkyl amine derivatives are employed as sources of acyl carbon atoms and tert-butyl hydroperoxide is employed as the oxygen source of the acyl group.
引用
收藏
页码:470 / 474
页数:5
相关论文
共 27 条
[1]   Metal-catalysed approaches to amide bond formation [J].
Allen, C. Liana ;
Williams, Jonathan M. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415
[2]   Flower-like AgNPs@m-MgO as an excellent catalyst for CO2 fixation and acylation reactions under ambient conditions [J].
Chowdhury, Arpita Hazra ;
Ghosh, Swarbhanu ;
Islam, Sk. Manirul .
NEW JOURNAL OF CHEMISTRY, 2018, 42 (17) :14194-14202
[3]   Sunlight assisted direct amide formation via a charge-transfer complex [J].
Cohen, Irit ;
Mishra, Abhaya K. ;
Parvari, Galit ;
Edrei, Rachel ;
Dantus, Mauricio ;
Eichen, Yoav ;
Szpilman, Alex M. .
CHEMICAL COMMUNICATIONS, 2017, 53 (73) :10128-10131
[4]   Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Alkyl Bromides: Et3N as the Terminal Reductant [J].
Duan, Zhengli ;
Li, Wu ;
Lei, Aiwen .
ORGANIC LETTERS, 2016, 18 (16) :4012-4015
[5]   Direct synthesis of 2-methylpyridines via I2-triggered [3+2+1] annulation of aryl methyl ketoxime acetates with triethylamine as the carbon source [J].
Gao, Qinghe ;
Yan, Huijuan ;
Wu, Manman ;
Sun, Jiajia ;
Yan, Xiqing ;
Wu, Anxin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (13) :2342-2348
[6]   Mechanoenzymatic peptide and amide bond formation [J].
Hernandez, Jose G. ;
Ardila-Fierro, Karen J. ;
Crawford, Deborah ;
James, Stuart L. ;
Bolm, Carsten .
GREEN CHEMISTRY, 2017, 19 (11) :2620-2625
[7]   Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis [J].
Hu, Long ;
Xu, Silin ;
Zhao, Zhenguang ;
Yang, Yang ;
Peng, Zhiyuan ;
Yang, Ming ;
Wang, Changliu ;
Zhao, Junfeng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (40) :13135-13138
[8]   The amide C-N bond of isatins as the directing group and the internal oxidant in Ru-catalyzed C-H activation and annulation reactions: access to 8-amido isocoumarins [J].
Kaishap, Partha Pratim ;
Sarma, Bipul ;
Gogoi, Sanjib .
CHEMICAL COMMUNICATIONS, 2016, 52 (63) :9809-9812
[9]   Unprecedented conversion of triethylamine and disulfur dichloride into a thienopentathiepin and a heptathiocane [J].
Konstantinova, LS ;
Rakitin, OA ;
Rees, CW ;
Souvorova, LI ;
Golovanov, DG ;
Lyssenko, KA .
ORGANIC LETTERS, 2003, 5 (11) :1939-1942
[10]   A novel silver nanoparticle embedded mesoporous polyaniline (mPANI/Ag) nanocomposite as a recyclable catalyst in the acylation of amines and alcohols under solvent free conditions [J].
Mandi, Usha ;
Roy, Anupam Singha ;
Banerjee, Biplab ;
Islam, Sk. Manirul .
RSC ADVANCES, 2014, 4 (80) :42670-42681